<!DOCTYPE html>
<html>
<head>
<meta charset="UTF-8">
<title>Cover Up Housekeeper by Hopefultoahappyplace</title>
<style type="text/css">

body { background-color: #ffffff; }
.CI {
text-align:center;
margin-top:0px;
margin-bottom:0px;
padding:0px;
}
.center   {text-align: center;}
.cover    {text-align: center;}
.full     {width: 100%; }
.quarter  {width: 25%; }
.smcap    {font-variant: small-caps;}
.u        {text-decoration: underline;}
.bold     {font-weight: bold;}
</style>
</head>
<body>
<h1><a href="https://archiveofourown.org/works/24326722">Cover Up Housekeeper</a> by <a class='authorlink' href='https://archiveofourown.org/users/Hopefultoahappyplace/pseuds/Hopefultoahappyplace'>Hopefultoahappyplace</a></h1>

<table class="full">

<tr><td><b>Category:</b></td><td>Naruto</td></tr>

<tr><td><b>Genre:</b></td><td>M/M, One Shot, One Shot Collection, Other, Smut</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-05-22</td></tr>

<tr><td><b>Updated:</b></td><td>2020-05-22</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-04 05:40:20</td></tr>

<tr><td><b>Rating:</b></td><td>Explicit</td></tr>

<tr><td><b>Warnings:</b></td><td>Creator Chose Not To Use Archive Warnings</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>3,963</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/24326722</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/Hopefultoahappyplace/pseuds/Hopefultoahappyplace</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>Itachi was bored of his everyday life. He found himself repeating the same days over and over. As he was suddenly giving a strange job offer from an article man, he was willing to take a change with it.</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Uchiha Itachi/Uchiha Madara</td></tr>

<tr><td><b>Comments:</b></td><td>2</td></tr>

<tr><td><b>Kudos:</b></td><td>18</td></tr>

</table>

<a name="section0001"><h2>Cover Up Housekeeper</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Author's Note:</b><blockquote class="userstuff">
      <p>Itachi here is female to Male transgender to avoid any confusion.</p><p>This is my first work in a very long time, so if this goes well I'll consider more chapters</p>
    </blockquote></div><div class="userstuff module">
    
    <p>"Work for me"<br/>
The words came as a shock for Itachi. He had only just met this man. It wasn't a request, it wasn't a demand. It was as if he had handed a ball to him and left Itachi to decide what to do with it. He had accidentally bumped into the man as he was reaching for rice at the grocery store, "oh I'm sorry, I didn't see you there" he meant to only glance at the man, not wanting to make a big deal out of their encounter.<br/>
"Don't even worry about it"<br/>
But there was something off about the man. But was ' off '  the right term he should be using. He was more enchanted by him. That was purely the only reason for responding after the man said,<br/>
"Say, how familiar are you with the city? I just moved here, I would like to get to know this place more."<br/>
It was simple enough, right? "I've lived here my whole life. I know the city like the back of my hand" but why was he talking to him. Itachi never talks to people. But his appearance was unique, and caught his eye. Long black, untamed hair that seemed spiky. Itachi was almost jealous. He had a broad, muscular build that complimented his face.<br/>
"Very good" was that a praise "I have an open position I would like you to fill" he dug in his pocket for his wallet, he opened it up and grabbed a small card and held it out for Itachi "work for me"<br/>
"Wait" that was too much, too fast, "I thought you wanted to get to know the city"<br/>
"I do, but I have a good feeling about you. I can pay you better and it isn't hard work, in my opinion. Give me a call if you're interested."<br/>
Just like that the man walked away. Leaving Itachi dumbfounded in the middle of the aisle. He looked down down at the card, looking to see if it was legit<br/>
The Akatsuki<br/>
Make the world better is no longer an illusion<br/>
×××.×××.××××</p><p>Itachi was alone, sitting at the table of his small apartment staring at the small piece of paper. It had been a day after that strange incident. He tried to forget it even happened, but he only spent the whole day thinking about it. If he was being honest with himself, he needed a change in his life. After his parents death there wasn't anything new in his life. His brother was gone in the military so they spoke every other day, but he was just bored. </p><p>Everyday it seemed he woke up, went to work, came back home and slept. That man he had met gave a deep feeling of excitement that he hadn't felt in a very long time. He wondered if this strange man could fulfill this empty hole in his life.</p><p>The other part of him was truly scared. So many what if‘s plagued his head. His job was stable and paid decently. If he gave it up, he wouldn't be able to get it back.</p><p>'But.. it wouldn't hurt just to try, right?' Was his thought as he dial the phone number. His teeth were pressing into his lip as his leg bounced. </p><p>"Hello, this is the Akatsuki Agency" a familiar voice spoke through the phone </p><p>"Hello um," how does he introduce himself, they never exchange names, "we spoke in the grocery store the other day. You offered me a job and gave me your card" his voice sounded too nervous for his liking, but he did hate this part of the job search.</p><p>"Ah yes, I was hoping to hear from you"</p><p>"Yes I was wanting to know more about this job offer you have" </p><p>"Well essentially, the position I had in mind is a mix of my assistant and maid work" </p><p>"Maid work?" Itachi looked at the phone as if it done him wrong </p><p>"Ya know, clean my office, clean my room. Nothing disgusting. I am horrible at keeping my space clean. But I am willing to top your pay. I am hoping you will take my offer" </p><p>"Well," itachi was confused as to why he wanted him so much, "why do want me to work for you, not to sound rude" he was just some guy he bumped into at the store. Wouldn't it be better if the man hired a professional cleaner? </p><p>"You see, I've been rather bored. You seem like the perfect person to make work just a little fun" the man's voice sounded more silky than before. </p><p>"How do you know if I'm exciting enough for you"</p><p>"Why don't you come in tomorrow for an interview, we can see how fun you can be" </p><p>Shivers ran through Itachi's body, he was almost certain this man was flirting with him, but that would be unprofessional. "What time?" that didn't bother him too much </p><p>"Let's do" there was a few papers filling around and then a sound of something metal falling on the floor, "let's do 9" </p><p>"that sounds good." A smile slowly formed on Itachi's face, "I’m Itachi, what's your name?"</p><p>"Itachi Hmm? I like that name. I'm Madara. The address is on our website, I don't know it by heart. But, I'll be waiting for you" </p><p>The line went quiet, the only thing Itachi heard was the beating of his own heart. He got up from the table. He figured now would be the best time to go to bed and to get up bright and early. But he was making an excuse for himself as he got undressed. </p><p>There hasn't been many times he found himself going into the bottom drawer of his nightstand, but tonight was one of them. Madara's voice kept running through his head as his fingers wrapped around a large purple dildo. He wanted nothing more than to have Madara bend him over a desk, taking him while talking dirty to him in his ear. He sat in the middle of the bed, rubbing the toy against his pussy as he rocked his hips against it. He loved the contrast his pussy and the dildo had. His pussy was small and pink, the dildo was large and a dark purple. He teased himself before sitting on the large dildo. It wasn't as good as sex, but it was enough for him and his obviously messed up hormones. </p><p>When he was done, he cleaned up and was actually going to bed this time. Very satisfied. </p><p> </p><p>It was 8:30 and itachi was parked outside of what seemed to be a mansion and not at all a place of business. He dialed the number that was now saved on his phone.</p><p>"Hello, this is the Akatsuki Agency"</p><p>"This is itachi, I'm here but I think I'm at the wrong place. This place is mansion"</p><p>"Are there black and red flowers by the door" </p><p>"Yes there is" </p><p>"Great, I'll send someone down for you" and he hung up.</p><p>Itachi wasn't too sure how to handle this. Working for some rich guy at his house as not only a maid but an assistant. Seems too much like a porn cliche. And he refuses to be a porn cliche. Even if he had full intentions of flirting with him before he even got the job. </p><p>It wasn't long before a blond guy with hair that looked as big as the attitude on his face came from the front door, approaching him. Itachi had to remind himself not to judge people too quickly.</p><p>"Ok come follow me. I'll take you to boss" his eyes rolled and looked as if he couldn't be bothered with anything and just started walking off. </p><p>"Thank you for taking me" Itachi just held his breath and followed. They walked quite a distance, he was sure he passed two entryways and came up three staircases. This place was huge. He was honestly worried that if he lost sight of this blond guy that he would get lost. Most of what he saw was empty. It was naked a canvas ready to get painted. It was two more long hallways before the guy stopped outside two very large french doors that looked like works of art. </p><p>The guy knocked on the door, "hey Madara, he's here!" He shouted, "Wait here" and then he walked off.  </p><p>Itachi looked around at the wall detailing. It looks expensive, like everything else in the house. </p><p>The doors opened inward with madara in the middle. "Hello, Itachi" he held his hand out. Madara was shamelessly wearing a tee-shirt and sweats. </p><p>Itachi shook his hand, feeling a little overdressed, having a button up shirt with a crew neck sweater and slacks, "Good morning". Madara gestures Itachi in the large room, "So this is your office?" He looked around in awe "This is easily more than half of my apartment size". Itachi didn't have a small apartment because he couldn't afford any better. He figured since he never needed any more space, there was no need to pay for it. But that didn't stop him from being amazed at the sheer size of everything. The room itself had only a large desk that was centered with ceiling high empty bookcases. He assumed the books may be inside the many boxes inside the room. </p><p>Madara chuckled a bit "Yes, well I need the space. So shall we get in with the interview?" Itachi nodded his head, "well I'd have to apologize. I would offer you a place to sit. The lovely assistant who brought you here decided not to order any seating at all except for my chair" it was quite obvious he was annoyed. </p><p>"You mean no other seating in this entire mansion or this room?" </p><p>"The entire mansion" he pushed some papers to the side and sat on the edge of his desk. "But to be honest I don't really do interviews" he laughed at the face itachi made, which was a very confused one. "I just wanted you to come in. For all I care you're hired"</p><p>"Wait what? Why did you tell me to come in" he could tell this man was unorganized </p><p>"I just wanted to see you" the words came out casually and his eyes looked Itachi up and down. </p><p>That shiver ran through him much harder than it did last night. He needed to ignore that "So, what will I be doing today?" </p><p>"I can give you a walkthrough on what a normal work day will look like" </p><p>"I would like that" Itachi was relieved, he felt like he was finally getting somewhere. He was really hoping this job would work out, his other one was too strict and demanding.</p><p>"Alright, I hope this doesn't scare you off. But here" he grabbed a bag "it's a highly recommended, but required, uniform. You could put it on if you like" the smirk on his face made it obvious he was up to no good. </p><p>Itachi looked in the bag anyway, only to get an eyebrow bend real high on his head. It was a slutty maid's outfit that looked like it was going to where near his knees, "how much does pay start?" </p><p>"Name your price" </p><p>"30 an hour?" </p><p>"You better be one hell of organizer" </p><p>Itachi was in shock, he would never have gotten to that rate at his job. His old job, he was definitely quitting. With that pay, and he gets to wear a maid outfit, where has this man been. "Is there a bathroom where I can put this on?"</p><p>"I'll take that as a yes", itachi nodded quickly, "great, follow me" he got up from the table and walked out the room, guiding itachi a couple of  doors down to a large marble bathroom. "Knock yourself out. I normally don't allow anyone in this bathroom, so don't tell anyone"</p><p>Itachi walked in, holding back his 'wow'. The bathroom was by far the most beautiful he had been. He got in the bathroom and closed the door. He set the bag on the counter and laid out all the clothes: the short dress, the half apron, stockings, garter, thong that clearly meant for a man with a penis. Itachi was highly impressed at the level of perverson this man had. He undressed to his panties, very glad he wore his pink lace ones. He put the dress on and looked at himself in the mirror. The dress was very flattering on him, even if it was slutty. It barely covered his ass, but it fit his body nicely. He put the stockings on, but he didn't like how it looked on him, so he took them off. He put the apron on and the garter. It really put the outfit together.</p><p>Itachi stepped out into the hallways with the bag of his clothes in his hand. Madara was leaning on the wall, patiently waiting for him. "Wow, I didn't think it would look so great on you" he blew a whistle </p><p>Itachi's cheeks turned pink, "if I didn't know any better this would be an act of sexual harassment in a workplace" </p><p>"Oh most definitely" he replied as if it were nothing, "but I don't think you would have put on the outfit if you were worried about that"</p><p>Itachi smirked, he really wanted to tear his clothes off, "touché, what's first on the list of my job training?". </p><p>Madara pushed himself off the wall with a smile on his face and walked back into the office, "I would love it if you could move my books from the boxes on to the shelves" he motioned from the taped up box’s to the high shelves with a rolling ladder. </p><p>It was clear Madara wanted nothing more than to just see up Itachi's dress. This game of beating around the Bush was driving itachi insane. He rocked his hips, playing along with him, "easy enough". He walked over to the box and tore off the tape. Much to his surprise the box wasn't dusty, and neither were the books inside. It seemed that they made a quick move. He grabbed a few books and looked up, "Anywhere specific you want the books?" He turned to Madara, who was shamelessly staring at Itachi's ass.</p><p>He shoots his head up "No not really, one day I would like them alphabetized, but for now I just need these boxes out of here." </p><p>Itachi nodded his head as he walked to the ladder. Rocking it to see how sturdy it was. He figured it would be best to work top to bottom. He climbed up only a few steps, not liking the way it rocked but knew he was safe. If anything he would just fall on madara, who already made his way to the base of the ladder, keeping it from rocking. "I'm going to have to get this ladder adjusted, I would hate to see you fall" his hand finding its way on Itachi's calf, rubbing it. "Your skin is soft'' He looked up at the teasing snip of Itachi's lace panties.</p><p>"I would hate to fall as well," he got up on his toes to put the books on the shelf, one by one, not wanting to move away from his touch, "but I'm sure you would catch me?" He looked down at him with heat in his eyes.</p><p>"Of course I would, I'm not a monster" his hand went further up as Itachi went down a step. His hand gripped and massaged itachi's thigh, "I wouldn't want you to bruise your skin" his hand inched up with every word. </p><p>Itachi bit his lip and arched his back, popping his ass out more than it did on it's own. "You're so caring, how did I run into a boss like you". He wanted him so bad, so many thoughts raced through his head. The fact that his pussy was getting his panties wet kept coming to mind. Or the fact that his new boss's giant hand was so close to feeling his wet panties. </p><p>"I care about all my workers'' His hand felt over Itachi's ass, causing him to gasp quietly, "Especially the ones who work close to me" he didn't want to take it slow anymore, Madara was fully aware that they both were craving  each other. His hand moved down and rubbed at his pussy lightly, "you're wet Itachi" he leaned forward and kissed his thighs. </p><p>Itachi breath hitched. He didn't actually think this would come so soon, and not so straightforward, "I've been like that since I walked in" his fists were white from gripping the ladder, all the books now put up. </p><p>"I apologize, I cant let my employee go unsatisfied" his hand glided over Itachi's skin before slowly pulling down his panties. He watched a string precum connecting his pussy to the panties stretched and broke. "Do not hesitate to tell me you need to be satisfied" he picked Itachi's foot up to take his panties off one leg </p><p>"Yes sir" he was breathless, he couldn't believe this was actually happening. He let out a loud gasp as he felt a wet tongue rub against his pussy. "Oh my god" it had been so long and it felt so good. He spread his legs, giving him all the access he wanted. </p><p>Madara was enjoying himself, he wasn't expecting him to taste so good. It was as if he was licking up a thick mango juice. The way Itachi was wriggling and moaning above him, was really making him want to try his luck. </p><p>Itachi nearly lost it when he felt that amazing tongue slide inside of him. His knees wanted to cave in on him, "i-i need to get down" he panted out in a hurry "it's too much up here" even if he was having the time of his life, I would hate to actually end up falling, now that there was actually a risk. </p><p>Madara reluctantly moved away from him to allow him to get down. He watched as his shaky legs moved down each step. He looked at his desk, messy with papers and shrugged to himself. It was already a mess, he grabbed the papers in a messy pile and dropped it on the floor.</p><p> Itachi had walked up behind him, "what are you doing" he didn't want to look impatient, but he wanted his face down in between his legs again. </p><p>Madara just turned to him, lust heavy in his eyes. He grabbed him by his small waist, picking him up and putting him on the desk. He took a moment to think about how much of a fucking genius he was to get a deal that gave him perfect access to him.</p><p>Itachi kicked off his panties to the side and hurried to undo Madara's pants. When he got it done, an uncertain feeling of anxiety rushed to his body, "if you're going to be my boss… isn't this inappropriate?" His whole demeanor changed in a matter of seconds, legs closed and an arm over his chest, eyebrows bunched together and eye darting around. </p><p>"I say we came this far, it wouldn't really matter. But if you're uncomfortable with this" he stepped back, "I'm not going to force you to do anything" </p><p>"It's.." itachi looked at him "it's not that I don't want to… I mean, I really do want to. But what if we get in trouble" </p><p>Madara smiled and rubbed his legs while leaning in towards his ear, "That sounds like it's going to have to be our little secret right?" </p><p>Itachi nodded his head, "sounds like a great plan" he wrapped his legs around the bigger man "sorry about that"</p><p>"No no" he brushed some hair from itachi's face to behind his ear, "I want to make sure you are 100 percent comfortable with me when I fuck you against the desk". </p><p>A lighthearted laugh came from itachi, "I'm all open for you" he licked against his bottom lip, starting a long, lustful kiss. Madara slowly rubbed his tip against itachi's clit before slowly thrusting inside. Itachi head fell back, "wow" he ran his fingers through his hair </p><p>"Don't get too comfortable" he gave one teasing thrust "I haven't even gotten started" he put his wide hand on itachi's stomach, guiding him to lay down. The worst he can do is crumble paper that has already been crumbled. </p><p>Itachi's eyes were half open as he looked up at him with anticipation. "Don't make me wait" Itachi surprised himself of his overwhelming need for the other man. He couldn't remember when he was last intimate with someone. He was thankful that his long wait was coming to an end. </p><p>A long and low groan escaped both of their mouths when madara started to slide into Itachi's warm pussy.  He held a tight grip on Itachi's hips, holding his much smaller body in place as he started a steady pace. The intense soft grip around his member made him worry how long he would be able to hold out. A weak feeling came to his joints as he watched itachi's body shake and his hair bounce with each trust. His mouth hung open with a stream of moans coming from his soft, rosy lips. </p><p>Meanwhile, Itachi was having the time of his life. He was embarrassed by the vulgar noises his body was making, but it excited him as much as it embarrassed him. The electricity in his body ran wild with each thrust sending him wild. </p><p>It wasn't long before they finished. The exhilaration if it all weighted over their normal stamina. Madara sat down in his chair as itachi sat up on the desk. He swung his legs softly as he ran his fingers through his now messy hair at an attempt to fix it. "That was uh" he huffed out a breath of air as a replacement for his loss of words.</p><p>Madara nodded his head with agreement. He enjoyed himself a lot more than he thought he would, "how long will it be till you can start working" he must have regained some life into his knees since he got up and cleaned up the mess.</p><p>Itachi smiled softly as he looked for where he left his bag of proper clothing, "as soon as you can fill out the paperwork" he grabbed the bag that sat by the door and changed out his attire. "What would my job title be?" </p><p>A chuckle came from madara, which made itachi look over to him, "I have half a mind my label you a mistress, but for formality sake, it will have to be housekeeper" </p><p>"My job will be to make sure this building stays clean," he walked up to the man, then fixed his clothes as he admire his taller physique, "but then I have a suggested duty to make sure your day remains fully relived?"</p><p>"Exactly" his rough hand gripped at itachi's ass, "I'll call you when the paperwork is done" </p><p>He rolled his hips against his hand, "sounds like a plan" he knew he was going to have to leave soon. He was getting heated again, and he won't be able to last another round. "Don't tell the other employees?"</p><p>"Of course not. Don't need them thinking this behavior is appropriate" they both laughed. They said their goodbyes and itachi left for home.</p><p>He thought how amazing this new step in his life will be. He wasn't sure how everything would go. He would normally stress over not knowing. But things were different now. But there was one thing he knew for sure, and it was that there will be plenty of sex heading his way.</p>
  </div></div>
</body>
</html>